A tropical massage with a butt play chaser!

I had my first massage on vacation in the caribbean. My girlfriends and I planned a girls trip for a week. While there, my friends had shopping on the agenda each day. I'm not a shopaholic so when I was looking over things to do I saw massage offered so I ordered it up during the time they shopped. When I went to the spa room a big black woman greeted me. She was tall, full-figured and very dark. Older and attractive in a weird way (I'm not a lesbo or bi). I told her I'd never been massaged so I didn't know what to ask for, just something to help me relax and feel good. She slathered on the oil and worked on my back, butt and legs. She massaged my glutes and occasionally my cheeks would get spread apart. I didn't know if this was normal but I went with it.

When I turned over, she gave me a thorough massage including my breasts. Kneading them and rubbing my nipples. It was very professional and face up I could see that she wasn't acting creepy at all. Working my legs, she moved up my thighs and as she kneaded them her fingers would pass over my pussy lips but that was all. When she was done, I felt great but also a little horney and I went to my room and masturbated. Six months later, I took the same trip with my mother and sister. On a long shot, I booked a massage and sure enough it was the same woman. I said I thought I had been to her before but she didn't acknowledge me.

I got the same sort of massage but when she was kneading my buttocks I wiggled my butt slightly and let my legs part a little. She spent more time than she'd done before and this time I was sure she was deliberately slipping her fingers between my ass crack. When I flipped over she did a thorough massage but spent the most time on my boobs. When she worked my legs again she let her fingers touch my pussy lips and I sighed a little and let my legs part a little. I booked another massage for the next day and once again got the same professional but intimate massage. I made my motions and sounds a little more obvious hoping she'd interpret it as permission to go further. Still, it only went so far.

The next day I booked another massage and told her it was my final day there and she said she had a cancellation and would give me a little extra time. Sure enough as she massaged my butt she was definitely spreading my ass cheeks apart wide and ran her fingers from top to bottom over my asshole, labia and clit. When I flipped over she began with my face and neck, then my arms and asked if I was okay with my face and eyes covered. I nodded and she put a warm wet towel over my head and eyes (It felt amazing!!) and then began massaging my boobs. It was much more intimate this time as she pulled and pinched my nipples.

She moved to my side and was stroking my stomach, then I felt her lips and tongue on my nipples. She kneaded and sucked on them until I was sighing. She then took the towel (that was starting to cool) off my face and moved down to my feet. She knew I didn't care for foot massage and quickly moved up to my calves, then my thighs. She let her fingers graze over my labia and I let my legs fall wide apart. She started rubbing my labia and clit in earnest with one hand and used the other to slide her fingers into my vagina and butthole. Fucking me furiously she bent down and began licking and sucking my clit and I came hard.

She asked if I minded flipping over again and asked me to stay up on my knees but rest my arms and head on the table, my ass sticking up in the air. She was rubbing my lower back and the backs of my thighs before she started rubbing my pussy again concentrating on my clit. She was pressing my butt hole with her other hand and started slipping one finger inside me. Rubbing my clit and finger fucking my butt I came again quickly. Then I could feel her bending over me and she was running her tongue between my ass cheeks, then poked her tongue inside my butt fucking me that way. I had never had anything like that (and didn't know a tongue could be that long!) and came again but she didn't stop until I had orgasmed yet again. She had me stretch out and placed a warm blanket completely over me and told me I was welcome to lay there as long as I needed and to feel free to shower if I wanted. I think I actually dozed off a little, then got up wiped my body down, got dressed and left her a 100% tip.

I suggested the same trip to my girlfriends again the following year but they wanted a new destination. I begged off and went back to the same island and the same masseuse. I love that it's all been unspoken, intimate but professional if that makes sense. She never encourages me to do a thing. It's all her working on me. It all feels amazing but I will say this..... that woman loves licking assholes and I gotta say for a former ass play virgin, I'm all in!

(I've gotta find a butt licking fan closer to home!)

Related Posts

More Related Posts